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Volumn 46, Issue 48, 2005, Pages 8289-8292

Iodine-mediated Z-selective oxidation of ketones to α,β- unsaturated esters: Synthesis and mechanistic studies

Author keywords

Acrylates; Iodine; Oxidation

Indexed keywords

ESTER DERIVATIVE; IODINE; KETONE DERIVATIVE;

EID: 27644439820     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.176     Document Type: Article
Times cited : (12)

References (31)
  • 2
    • 0001937839 scopus 로고
    • For example, the use of phosphonoacetate reagents for the synthesis of Z-2,3-trisubstituted acrylates is hampered by the susceptibility of the products to isomerization under the reaction conditions; see W.S. Wadsworth Jr., and W.D. Emmons Org. Synth. 45 1965 44
    • (1965) Org. Synth. , vol.45 , pp. 44
    • Wadsworth Jr., W.S.1    Emmons, W.D.2
  • 15
    • 27644432054 scopus 로고    scopus 로고
    • note
    • For an exception, see Ref. 2c,d. No selectivity is observed under these conditions.
  • 18
    • 27644554993 scopus 로고    scopus 로고
    • Japanese Patent # JP60028950; 1985.
    • Japanese Patent # JP60028950; 1985.
  • 20
    • 27644511799 scopus 로고    scopus 로고
    • note
    • 3, 400 MHz): δ 167.8, 141.6, 140.0, 139.2, 131.6, 128.7, 128.5, 128.5, 128.3, 126.2, 126.2, 51.3, 40.4, 35.8.
  • 23
    • 0037272496 scopus 로고    scopus 로고
    • 13C data agrees well with known data for 2,4-diiodo-3-pentanone: see A.M. Montaňa, and P.M. Grima Synth. Commun. 33 2003 265 279
    • (2003) Synth. Commun. , vol.33 , pp. 265-279
    • Montaňa, A.M.1    Grima, P.M.2
  • 24
    • 27644593150 scopus 로고
    • For a similar isomerization, see: C. Rappe Acta Chem. Scand. 17 1963 2140
    • (1963) Acta Chem. Scand. , vol.17 , pp. 2140
    • Rappe, C.1
  • 27
    • 27644476449 scopus 로고    scopus 로고
    • note
    • 2. This assumption was affirmed when the reaction was run to 50% conversion and NMR data indicated only 20% D incorporation into the unreacted ketone.
  • 28
    • 27644498326 scopus 로고
    • For related studies on isolated cyclopropane systems, see: J.-M. Conia, and L. Blanco New J. Chem. 7 1983 399
    • (1983) New J. Chem. , vol.7 , pp. 399
    • Conia, J.-M.1    Blanco, L.2
  • 31
    • 0004035157 scopus 로고
    • R.A. Abramovich Plenum New York Chapter 6. The stereochemistry of 30 according to the Woodward-Hoffmann rules (see, Refs. 12, 14a)
    • For a review of the mechanism of the Favorskii rearrangement, see: (a) A. Baretta, and B. Waegell R.A. Abramovich Reactive Intermediates Vol. 2 1982 Plenum New York Chapter 6. The stereochemistry of 29 is speculated, but implied by the presumed stereochemistry of 30 according to the Woodward-Hoffmann rules (see, Refs. 12, 14a )
    • (1982) Reactive Intermediates , vol.2
    • Baretta, A.1    Waegell, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.